Hydrochloric Acid → HCID 46932147, compound

To a solution of 1-(5-chloro-4-nitro-2-thienyl)-3-dimethylamino-propan-1-one hydrochloride salt from the above (0.180 g, 0.687 mmol) and 2,4-dichlorobenzenethiol (0.123 g, 0.687 mmol) in N,N-dimethylformide (3 mL), was added potassium carbonate (0.237 g, 1.71 mmol). The resulting reaction mixture was stirred at ambient temperature for 5 hours. After this time, the reaction mixture was quenched with ice water and stirred at room temperature for 20 min and the precipitate which formed was collected by filtration and washed with water, and dried under vacuum. The crude solid was purified by silica gel chromatography to afford a yellow solid. The resulting solid was treated with hydrochloric acid (2 M). The solution was concentrated and dried under vacuum to afford the corresponding hydrochloride salt of the title product (90 mg, 17% yield). 1H NMR (400 MHz, MeOD) δ: 8.61 (1H, s), 8.05 (1H, m), 7.98 (1H, dd), 7.72 (1H, dd), 3.48 (2H, m), 3.33 (2H, m), 2.78 (3H, s). MS m/z: 404.9 [M+H]+.

1. customThe resulting reaction mixture
2. customAfter this time, the reaction mixture was quenched with ice water
3. stirringstirred at room temperature for 20 min
4. customthe precipitate which formed
5. filtrationwas collected by filtration
6. washwashed with water
7. customdried under vacuum
8. customThe crude solid was purified by silica gel chromatography
9. customto afford a yellow solid
10. concentrationThe solution was concentrated
11. customdried under vacuum

ORD record

ord-ce370b9210494da481b9f3b6ef71a8da

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680139B2